Dimethyltryptamine

Dimethyltryptamine
Clinical data
Other names	Dimethyltryptamine; DMT; N,N-DMT
Routes of; administration	By mouth (usually with an MAOI), inhalation, insufflation, rectal, intramuscular, intravenous
Drug class	Serotonergic psychedelic (hallucinogen)
ATC code	None;
Physiological data
Source tissues	Central nervous system (exact source tissues are not fully established)
Target tissues	Central nervous system
Receptors	At least 13 receptors (e.g., serotonin, sigma, trace amine-associated)
Precursor	Tryptophan
Metabolism	Oxidative deamination (MAO-A), N-oxidation, N-demethylation, peroxidation
Legal status
Legal status	AU: S9 (Prohibited substance) ; BR: F2 ; CA: Schedule III ; DE: Anlage I (Authorized scientific use only) ; UK: Class A ; US: Schedule I ; UN: Psychotropic Schedule I ;
Pharmacokinetic data
Bioavailability	Very low and inactive (except with an MAOI)
Metabolism	Oxidative deamination (MAO-A), N-oxidation, N-demethylation, peroxidation
Metabolites	Indole-3-acetic acid (NMT) (63–97%); DMT-N-oxide (DMT-NO) (3–28%); N-Methyltryptamine; Tryptamine; Others;
Onset of action	Inhalation: 10–15 seconds; Intravenous: ≤2–5 min; Intramuscular: 2–5 min; Oral with MAOI: ≤1 hour;
Elimination half-life	Alone: 5–15 min; With an MAOI: 1–4 hours;
Duration of action	Inhalation: ≤30 min; Intravenous: ≤30 min; Intramuscular: 30–60 min; Oral with MAOI: 4–6 hours;
Excretion	Urine
Identifiers
	IUPAC name 2-(1H-Indol-3-yl)-N,N-dimethylethanamine;
CAS Number	61-50-7 ;
PubChem CID	6089;
IUPHAR/BPS	141;
DrugBank	DB01488 ;
ChemSpider	5864 ;
UNII	WUB601BHAA;
KEGG	C08302 ;
ChEBI	CHEBI:28969 ;
ChEMBL	ChEMBL12420 ;
PDB ligand	A1AFV (PDBe, RCSB PDB);
CompTox Dashboard (EPA)	DTXSID60110053 ;
ECHA InfoCard	100.000.463
Chemical and physical data
Formula	C12H16N2
Molar mass	188.27 g·mol−1
3D model (JSmol)	Interactive image;
Density	1.099 g/cm3
Melting point	40 °C (104 °F)
Boiling point	160 °C (320 °F) at 0.6 Torr (80 Pa); also reported as; 80–135 °C (176–275 °F) at 0.03 Torr (4.0 Pa)
	SMILES CN(CCC1=CNC2=C1C=CC=C2)C;
	InChI InChI=1S/C12H16N2/c1-14(2)8-7-10-9-13-12-6-4-3-5-11(10)12/h3-6,9,13H,7-8H2,1-2H3 ; Key:DMULVCHRPCFFGV-UHFFFAOYSA-N ;
	(verify)

Dimethyltryptamine (DMT), also known as N,N-dimethyltryptamine (N,N-DMT), is a psychedelic drug from the tryptamine family that is found in nature in many plants and animals.^[1]^[2]^[3]^[9] DMT is used as a recreational drug and for spiritual reasons.^[10]

DMT works very quickly, has strong hallucinogenic effects, and works for only a few minutes. These reasons mean people in jobs such as businesspeople are known to use it.^[11] DMT can be inhaled or injected and its effects are different with different amounts used or different ways of taking it. When inhaled or injected, the effects last about five to fifteen minutes. Effects can last three hours or more when swallowed with a monoamine oxidase inhibitor (MAOI), such as ayahuasca used by Amazonian tribes.^[12] DMT causes effects that are hard to describe with words, such as very complex visual hallucinations (seeing things that are not there), changes to senses, ego death. DMT is is not addictive but can cause issues for the heart.

References

↑ ^1.00 ^1.01 ^1.02 ^1.03 ^1.04 ^1.05 ^1.06 ^1.07 ^1.08 ^1.09 ^1.10 Cameron LP, Olson DE (October 2018). "Dark Classics in Chemical Neuroscience: N, N-Dimethyltryptamine (DMT)". ACS Chem Neurosci. 9 (10): 2344–2357. doi:10.1021/acschemneuro.8b00101. PMID 30036036.
↑ ^2.00 ^2.01 ^2.02 ^2.03 ^2.04 ^2.05 ^2.06 ^2.07 ^2.08 ^2.09 ^2.10 ^2.11 Carbonaro TM, Gatch MB (September 2016). "Neuropharmacology of N,N-dimethyltryptamine". Brain Research Bulletin. 126 (Pt 1): 74–88. doi:10.1016/j.brainresbull.2016.04.016. PMC 5048497. PMID 27126737.
↑ ^3.0 ^3.1 ^3.2 ^3.3 ^3.4 ^3.5 ^3.6 ^3.7 ^3.8 Rodrigues AV, Almeida FJ, Vieira-Coelho MA (2019). "Dimethyltryptamine: Endogenous Role and Therapeutic Potential". J Psychoactive Drugs. 51 (4): 299–310. doi:10.1080/02791072.2019.1602291. hdl:10216/114373. PMID 31018803.
↑ ^4.00 ^4.01 ^4.02 ^4.03 ^4.04 ^4.05 ^4.06 ^4.07 ^4.08 ^4.09 Brito-da-Costa AM, Dias-da-Silva D, Gomes NG, Dinis-Oliveira RJ, Madureira-Carvalho Á (October 2020). "Toxicokinetics and Toxicodynamics of Ayahuasca Alkaloids N,N-Dimethyltryptamine (DMT), Harmine, Harmaline and Tetrahydroharmine: Clinical and Forensic Impact". Pharmaceuticals (Basel). 13 (11): 334. doi:10.3390/ph13110334. PMC 7690791. PMID 33114119.
↑ Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.
↑ Barker SA (June 2022). "Administration of N,N-dimethyltryptamine (DMT) in psychedelic therapeutics and research and the study of endogenous DMT". Psychopharmacology (Berl). 239 (6): 1749–1763. doi:10.1007/s00213-022-06065-0. PMC 8782705. PMID 35064294.
↑ Häfelinger G, Nimtz M, Horstmann V, Benz T (1999). "Untersuchungen zur Trifluoracetylierung der Methylderivate von Tryptamin und Serotonin mit verschiedenen Derivatisierungsreagentien: Synthesen, Spektroskopie sowie analytische Trennungen mittels Kapillar-GC" [Trifluoracetylation of methylated derivatives of tryptamine and serotonin by different reagents: synthesis, spectroscopic characterizations, and separations by capillary gas chromatography]. Zeitschrift für Naturforschung B. 54 (3): 397–414. doi:10.1515/znb-1999-0319. S2CID 101000504.
↑ Corothie E, Nakano T (May 1969). "Constituents of the bark of Virola sebifera". Planta Medica. 17 (2): 184–188. Bibcode:1969PlMed..17..184C. doi:10.1055/s-0028-1099844. PMID 5792479. S2CID 43312376.
↑ "Dimethyltryptamine". PubChem. U.S. National Library of Medicine. Retrieved 2025-05-22.
↑ McKenna DJ, Towers GH, Abbott F (April 1984). "Monoamine oxidase inhibitors in South American hallucinogenic plants: tryptamine and beta-carboline constituents of ayahuasca". Journal of Ethnopharmacology. 10 (2): 195–223. doi:10.1016/0378-8741(84)90003-5. PMID 6587171.
↑ Haroz R, Greenberg MI (November 2005). "Emerging drugs of abuse". The Medical Clinics of North America. 89 (6): 1259–1276. doi:10.1016/j.mcna.2005.06.008. OCLC 610327022. PMID 16227062.
↑ Pickover C (2005). Sex, Drugs, Einstein, and Elves: Sushi, Psychedelics, Parallel Universes, and the Quest for Transcendence. Smart Publications. ISBN 978-1-890572-17-4.

[CameronOlson2018-1] 1.00 ^1.01 ^1.02 ^1.03 ^1.04 ^1.05 ^1.06 ^1.07 ^1.08 ^1.09 ^1.10 Cameron LP, Olson DE (October 2018). "Dark Classics in Chemical Neuroscience: N, N-Dimethyltryptamine (DMT)". ACS Chem Neurosci. 9 (10): 2344–2357. doi:10.1021/acschemneuro.8b00101. PMID 30036036.

[CarbonaroGatch2016-2] 2.00 ^2.01 ^2.02 ^2.03 ^2.04 ^2.05 ^2.06 ^2.07 ^2.08 ^2.09 ^2.10 ^2.11 Carbonaro TM, Gatch MB (September 2016). "Neuropharmacology of N,N-dimethyltryptamine". Brain Research Bulletin. 126 (Pt 1): 74–88. doi:10.1016/j.brainresbull.2016.04.016. PMC 5048497. PMID 27126737.

[RodriguesAlmeidaVieira-Coelho2019-3] 3.0 ^3.1 ^3.2 ^3.3 ^3.4 ^3.5 ^3.6 ^3.7 ^3.8 Rodrigues AV, Almeida FJ, Vieira-Coelho MA (2019). "Dimethyltryptamine: Endogenous Role and Therapeutic Potential". J Psychoactive Drugs. 51 (4): 299–310. doi:10.1080/02791072.2019.1602291. hdl:10216/114373. PMID 31018803.

[Brito-da-CostaDias-da-SilvaGomes2020-4] 4.00 ^4.01 ^4.02 ^4.03 ^4.04 ^4.05 ^4.06 ^4.07 ^4.08 ^4.09 Brito-da-Costa AM, Dias-da-Silva D, Gomes NG, Dinis-Oliveira RJ, Madureira-Carvalho Á (October 2020). "Toxicokinetics and Toxicodynamics of Ayahuasca Alkaloids N,N-Dimethyltryptamine (DMT), Harmine, Harmaline and Tetrahydroharmine: Clinical and Forensic Impact". Pharmaceuticals (Basel). 13 (11): 334. doi:10.3390/ph13110334. PMC 7690791. PMID 33114119.

[5] Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.

[Barker2022-6] Barker SA (June 2022). "Administration of N,N-dimethyltryptamine (DMT) in psychedelic therapeutics and research and the study of endogenous DMT". Psychopharmacology (Berl). 239 (6): 1749–1763. doi:10.1007/s00213-022-06065-0. PMC 8782705. PMID 35064294.

[7] Häfelinger G, Nimtz M, Horstmann V, Benz T (1999). "Untersuchungen zur Trifluoracetylierung der Methylderivate von Tryptamin und Serotonin mit verschiedenen Derivatisierungsreagentien: Synthesen, Spektroskopie sowie analytische Trennungen mittels Kapillar-GC" [Trifluoracetylation of methylated derivatives of tryptamine and serotonin by different reagents: synthesis, spectroscopic characterizations, and separations by capillary gas chromatography]. Zeitschrift für Naturforschung B. 54 (3): 397–414. doi:10.1515/znb-1999-0319. S2CID 101000504.

[8] Corothie E, Nakano T (May 1969). "Constituents of the bark of Virola sebifera". Planta Medica. 17 (2): 184–188. Bibcode:1969PlMed..17..184C. doi:10.1055/s-0028-1099844. PMID 5792479. S2CID 43312376.

[9] "Dimethyltryptamine". PubChem. U.S. National Library of Medicine. Retrieved 2025-05-22.

[McKennaTowers1984-10] McKenna DJ, Towers GH, Abbott F (April 1984). "Monoamine oxidase inhibitors in South American hallucinogenic plants: tryptamine and beta-carboline constituents of ayahuasca". Journal of Ethnopharmacology. 10 (2): 195–223. doi:10.1016/0378-8741(84)90003-5. PMID 6587171.

[11] Haroz R, Greenberg MI (November 2005). "Emerging drugs of abuse". The Medical Clinics of North America. 89 (6): 1259–1276. doi:10.1016/j.mcna.2005.06.008. OCLC 610327022. PMID 16227062.

[Pickover_2005-12] Pickover C (2005). Sex, Drugs, Einstein, and Elves: Sushi, Psychedelics, Parallel Universes, and the Quest for Transcendence. Smart Publications. ISBN 978-1-890572-17-4.

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]

[9]

[10]

[11]

[12]